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Former UK prime minister Winston Churchill left school in 1893 at the age of 19, and immediately entered the military. Except it took him three attempts before he passed the entrance exam to the Royal Military College in Sandhurst, England.

Although Churchill was well paid as a second lieutenant in the 4th Hussars, he regularly overspent his salary, as well as a further and greater sum paid to him by his mother. In order to boost his income, Churchill began war correspondence for a range of London newspapers.

In 1895, Churchill was commissioned by London's Daily Graphic (now defunct) to write about the conflict between Spain and Cuban guerillas. This was to be a significant incident in the young Churchill's life for more than one reason. It was the first time he came under fire (for which he would receive a Spanish medal), and it also introduced Churchill to an object which would become his lifelong companion: the Havana cigar.

1899

Churchill during his service in the South African Light Horse.

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1897

Churchill on horseback in Bangalore, India.

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1900

Churchill standing at the opening of his tent as a war correspondent during the Second Boer War, in Bloemfontein, South Africa.